Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device

ABSTRACT

An organometallic compound represented by Formula 1: 
       M 1 (Ln 1 ) n1 (Ln 2 ) n2    
     wherein, in Formula 1, M 1  is a transition metal; Ln 1  is a ligand represented by Formula 1A; Ln 2  is a ligand represented by Formula 1B; n1 is 1 or 2; and n2 is 1 or 2, 
     
       
         
         
             
             
         
       
     
     wherein X 1  is C or N, X 2  is C or N, Y 2  is O or S, and the other substituents are as described in the detailed description.

CROSS-REFERENCE TO RELATED APPLICATION

This application is based on and claims priority to Korean PatentApplication No. 10-2021-0175922, filed on Dec. 9, 2021, in the KoreanIntellectual Property Office, and all the benefits accruing therefromunder 35 U.S.C. § 119, the content of which is incorporated by referenceherein in its entirety.

BACKGROUND 1. Field

The present subject matter relates to an organometallic compound, anorganic light-emitting device including the same, and an electronicapparatus including the organic light-emitting device.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emissive devices whichhave improved characteristics in terms of viewing angles, response time,luminance, driving voltage, and response speed. OLEDs can also producefull-color images.

OLEDs include an anode, a cathode, and an organic layer located betweenthe anode and the cathode, wherein the organic layer includes anemission layer. A hole transport region may be located between the anodeand the emission layer, and an electron transport region may be locatedbetween the emission layer and the cathode. Holes provided from theanode move toward the emission layer through the hole transport region,and electrons provided from the cathode move toward the emission layerthrough the electron transport region. The holes and the electronsrecombine in the emission layer to produce excitons. These excitonstransition from an excited state to a ground state, thereby generatinglight.

SUMMARY

Provided are an organometallic compound, an organic light-emittingdevice including the same, and an electronic apparatus including theorganic light-emitting device.

Additional aspects will be set forth in part in the detailed descriptionwhich follows and, in part, will be apparent from the detaileddescription, or may be learned by practice of the presented exemplaryembodiments.

According to an aspect, provided is an organometallic compoundrepresented by Formula 1:

wherein, in Formulae 1A and 1 B,

ring CY₁ and ring CY₂ are each independently a C₅-C₃₀ carbocyclic groupor a C₁-C₃₀ heterocyclic group,

ring CY₃ is a 6-membered heterocyclic group; a 6-membered heterocyclicgroup condensed with a C₅-C₃₀ carbocyclic group; or a 6-memberedheterocyclic group condensed with a C₁-C₃₀ heterocyclic group,

ring CY₄ is a 6-membered carbocyclic group; a 6-membered heterocyclicgroup; a 6-membered carbocyclic group condensed with a C₅-C₃₀carbocyclic group; a 6-membered carbocyclic group condensed with aC₁-C₃₀ heterocyclic group; a 6-membered heterocyclic group condensedwith a C₅-C₃₀ carbocyclic group; or a 6-membered heterocyclic groupcondensed with a C₁-C₃₀ heterocyclic group,

X₁ is C or N, and X₂ is C or N,

Y₂ is O or S,

R₁₀, R₂₀, R₃₀, and R₄₀ are each independently hydrogen, deuterium, —F,—Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₁-C₆₀ alkylthio group, a substituted or unsubstitutedC₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₇-C₆₀ alkyl aryl group, asubstituted or unsubstituted C₇-C₆₀ aryl alkyl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted C₂-C₆₀ alkyl heteroaryl group, asubstituted or unsubstituted C₂-C₆₀ heteroaryl alkyl group, asubstituted or unsubstituted C₁-C₆₀ heteroaryloxy group, a substitutedor unsubstituted C₁-C₆₀ heteroarylthio group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —Ge(Q₁)(Q₂)(Q₃), —N(Q₄)(Q₅),—B(Q₆)(Q₇), —P(Qs)(Q₉), or —P(═O)(Q₈)(Q₉),

neighboring two or more of a plurality of R₁₀ are optionally bondedtogether to form a substituted or unsubstituted C₅-C₃₀ carbocyclic groupor a substituted or unsubstituted C₁-C₃₀ heterocyclic group,

neighboring two or more of a plurality of R₂₀ are optionally bondedtogether to form a substituted or unsubstituted C₅-C₃₀ carbocyclic groupor a substituted or unsubstituted C₁-C₃₀ heterocyclic group,

neighboring two or more of a plurality of R₃₀ are optionally bondedtogether to form a substituted or unsubstituted C₅-C₃₀ carbocyclic groupor a substituted or unsubstituted C₁-C₃₀ heterocyclic group,

neighboring two or more of a plurality of R₄₀ are optionally bondedtogether to form a substituted or unsubstituted C₅-C₃₀ carbocyclic groupor a substituted or unsubstituted C₁-C₃₀ heterocyclic group,

neighboring two or more of R₁₀, R₂₀, R₃₀, and R₄₀ are optionally bondedtogether to form a substituted or unsubstituted C₅-C₃₀ carbocyclic groupor a substituted or unsubstituted C₁-C₃₀ heterocyclic group,

b10, b20, b30, and b40 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9,or 10,

* and *′ each indicate a binding site to M₁,

at least one substituent of the substituted C₅-C₃₀ carbocyclic group,the substituted C₁-C₃₀ heterocyclic group, the substituted C₁-C₆₀ alkylgroup, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substitutedC₁-C₆₀ alkylthio group, the substituted C₃-C₁₀ cycloalkyl group, thesubstituted C₁-C₁₀ heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenyl group, thesubstituted C₆-C₆₀ aryl group, the substituted C₇-C₆₀ alkyl aryl group,the substituted C₇-C₆₀ aryl alkyl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted C₂-C₆₀ alkyl heteroaryl group, thesubstituted C₂-C₆₀ heteroaryl alkyl group, the substituted C₁-C₆₀heteroaryloxy group, the substituted C₁-C₆₀ heteroarylthio group, thesubstituted monovalent non-aromatic condensed polycyclic group, and thesubstituted monovalent non-aromatic condensed heteropolycyclic group is:

deuterium, —F, —Cl, —Br, —I, —SF₅, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H,—CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group,an am idino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, or aC₁-C₆₀ alkylthio group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, or a C₁-C₆₀ alkylthio group, each substituted withat least one of deuterium, —F, —Cl, —Br, —I, —SF₅, —CD₃, —CD₂H, —CDH₂,—CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₇-C₆₀ alkylaryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a C₂-C₆₀ alkyl heteroaryl group, a C₁-C₆₀heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —Si(Qi₁)(Q₁₂)(Q₁₃),—Ge(C₂₁₁)(Q₁₂)(Q₁₃), —N(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), —P(Q₁₈)(Q₁₉),—P(=₀)(Q₁₈)(Q₁₉), or a combination thereof;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₇-C₆₀ alkyl aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀ heteroaryl group, a C₂-C₆₀ alkyl heteroarylgroup, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, amonovalent non-aromatic condensed polycyclic group, or a monovalentnon-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₇-C₆₀ alkyl aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀ heteroaryl group, a C₂-C₆₀ alkyl heteroarylgroup, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, amonovalent non-aromatic condensed polycyclic group, or a monovalentnon-aromatic condensed heteropolycyclic group, each substituted with atleast one of deuterium, —F, —Cl, —Br, —I, —SF₅, —CD₃, —CD₂H, —CDH₂,—CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxygroup, a C₁-C₆₀ alkylthio group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₇-C₆₀ alkyl arylgroup, a C₇-C₆₀ aryl alkyl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀ heteroaryl group, a C₂-C₆₀ alkyl heteroarylgroup, a C₂-C₆₀ heteroaryl alkyl group, a C₁-C₆₀ heteroaryloxy group, aC₁-C₆₀ heteroarylthio group, a monovalent non-aromatic condensedpolycyclic group, a monovalent non-aromatic condensed heteropolycyclicgroup, —Si(Q₂₁)(Q₂₂)(Q₂₃), —Ge(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₄)(Q₂₅),—B(Q₂₆)(Q₂₇), —P(Q₂₈)(Q₂₉), —P(—O)(Q₂₈)(Q₂₉), or a combination thereof;or

—Si(Q₃₁)(Q₃₂)(Q₃₃), —Ge(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇),—P(Q₃₈)(Q₃₉), or —P(=O)(Q₃₈)(Q₃₉), and

Q₁ to Q₉, Q₁₁ to Q₁₉, Q₂₁ to Q₂₉, and Q₃₁ to Q₃₉ are each independentlyhydrogen, deuterium, —F, —Cl, —Br, —SF₅, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an am idino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₁-C₆₀ alkylthiogroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted heterocycloalkenyl group, a substituted or unsubstitutedC₆-C₆₀ aryl group, a substituted or unsubstituted C₇-C₆₀ alkyl arylgroup, a substituted or unsubstituted C₇-C₆₀ aryl alkyl group, asubstituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted orunsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstitutedC₁-C₆₀ heteroaryl group, a substituted or unsubstituted C₂-C₆₀ alkylheteroaryl group, a substituted or unsubstituted C₂-C₆₀ heteroaryl alkylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryloxy group, asubstituted or unsubstituted C₁-C₆₀ heteroarylthio group, a substitutedor unsubstituted monovalent non-aromatic condensed polycyclic group, ora substituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group.

According to an aspect of another embodiment, provided is an organiclight-emitting device including: a first electrode; a second electrode;and an organic layer located between the first electrode and the secondelectrode, wherein the organic layer includes an emission layer, andwherein the organic layer further includes at least one of theorganometallic compound.

The organometallic compound may be included in the emission layer of theorganic layer, and the organometallic compound included in the emissionlayer may act as a dopant.

According to an aspect of another embodiment, provided is an electronicapparatus including the organic light-emitting device.

BRIEF DESCRIPTION OF THE DRAWING

The above and other aspects, features, and advantages of certainexemplary embodiments will be more apparent from the following detaileddescription taken in conjunction with the FIGURE, which is a schematiccross-sectional view showing an organic light-emitting device accordingto one or more embodiments.

DETAILED DESCRIPTION

Reference will now be made in further detail to exemplary embodiments,examples of which are illustrated in the accompanying drawing, whereinlike reference numerals refer to like elements throughout. In thisregard, the present exemplary embodiments may have different forms andshould not be construed as being limited to the detailed descriptionsset forth herein. Accordingly, the exemplary embodiments are merelydescribed in further detail below, and by referring to the figure, toexplain aspects.

The terminology used herein is for the purpose of describing one or moreexemplary embodiments only and is not intended to be limiting. As usedherein, the singular forms “a,” “an,” and “the” are intended to includethe plural forms as well, unless the context clearly indicatesotherwise. As used herein, the term “and/or” includes any and allcombinations of one or more of the associated listed items. The term“or” means “and/or.” Expressions such as “at least one of,” whenpreceding a list of elements, modify the entire list of elements and donot modify the individual elements of the list. It will be furtherunderstood that the terms “comprises” and/or “comprising,” or “includes”and/or “including” when used in this specification, specify the presenceof stated features, regions, integers, steps, operations, elements,and/or components, but do not preclude the presence or addition of oneor more other features, regions, integers, steps, operations, elements,components, and/or groups thereof.

The terminology used herein is for the purpose of describing one or moreexemplary embodiments only and is not intended to be limiting. As usedherein, the singular forms “a,” “an,” and “the” are intended to includethe plural forms as well, unless the context clearly indicatesotherwise. The term “or” means “and/or.” It will be further understoodthat the terms “comprises” and/or “comprising,” or “includes” and/or“including” when used in this specification, specify the presence ofstated features, regions, integers, steps, operations, elements, and/orcomponents, but do not preclude the presence or addition of one or moreother features, regions, integers, steps, operations, elements,components, and/or groups thereof.

It will be understood that, although the terms first, second, third etc.may be used herein to describe various elements, components, regions,layers, and/or sections, these elements, components, regions, layers,and/or sections should not be limited by these terms. These terms areonly used to distinguish one element, component, region, layer, orsection from another element, component, region, layer, or section.Thus, a first element, component, region, layer, or section discussedbelow could be termed a second element, component, region, layer, orsection without departing from the teachings of the present embodiments.

Exemplary embodiments are described herein with reference to crosssection illustrations that are schematic illustrations of idealizedembodiments. As such, variations from the shapes of the illustrations asa result, for example, of manufacturing techniques and/or tolerances,are to be expected. Thus, embodiments described herein should not beconstrued as limited to the particular shapes of regions as illustratedherein but are to include deviations in shapes that result, for example,from manufacturing. For example, a region illustrated or described asflat may, typically, have rough and/or nonlinear features. Moreover,sharp angles that are illustrated may be rounded. Thus, the regionsillustrated in the figures are schematic in nature and their shapes arenot intended to illustrate the precise shape of a region and are notintended to limit the scope of the present claims.

It will be understood that when an element is referred to as being “on”another element, it can be directly in contact with the other element orintervening elements may be present therebetween. In contrast, when anelement is referred to as being “directly on” another element, there areno intervening elements present.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this general inventive conceptbelongs. It will be further understood that terms, such as those definedin commonly used dictionaries, should be interpreted as having a meaningthat is consistent with their meaning in the context of the relevant artand the present disclosure, and will not be interpreted in an idealizedor overly formal sense unless expressly so defined herein.

“About” or “approximately” as used herein is inclusive of the statedvalue and means within an acceptable range of deviation for theparticular value as determined by one of ordinary skill in the art,considering the measurement in question and the error associated withmeasurement of the particular quantity (i.e., the limitations of themeasurement system). For example, “about” can mean within one or morestandard deviations, or within ±30%, 20%, 10%, 5% of the stated value.

Hereinafter, a work function or a highest occupied molecular orbital(HOMO) energy level is expressed as an absolute value from a vacuumlevel. In addition, when the work function or the HOMO energy level isreferred to be “deep,” “high” or “large,” the work function or the HOMOenergy level has a large absolute value based on “0 eV” of the vacuumlevel, while when the work function or the HOMO energy level is referredto be “shallow,” “low,” or “small,” the work function or HOMO energylevel has a small absolute value based on “0 eV” of the vacuum level.

An aspect provides an organometallic compound represented by Formula 1:

M₁(Ln₁)n₁(Ln₂)_(n2)   Formula 1

wherein, in Formula 1, M₁ is a transition metal.

For example, M₁ may be a Period 1 transition metal of the Periodic Tableof Elements, a Period 2 transition metal of the Periodic Table ofElements, or a Period 3 transition metal of the Periodic Table ofElements.

In one or more embodiments, M₁ may be iridium (Ir), platinum (Pt),osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu),terbium (Tb), thulium (Tm), or rhodium (Rh).

In one or more embodiments, M₁ may be Ir, Pt, Os, or Rh.

In one or more embodiments, M₁ may be Ir.

In Formula 1, n1 is 1 or 2, and n2 is 1 or 2.

In one or more embodiments, a sum of n1 and n2 may be 2 or 3.

In one or more embodiments, M₁ may be Ir, and a sum of n1 and n2 may be3.

In one or more embodiments, M₁ may be Pt, and a sum of n1 and n2 may be2.

Lni in Formula 1 is a ligand represented by Formula 1A:

wherein, in Formula 1A, X₁ is C or N, and X₂ is C or N.

Ring CY₁ and ring CY₂ in Formula 1A are each independently a C₅-C₃₀carbocyclic group or a C₁-C₃₀ heterocyclic group.

In one or more embodiments, ring CY₁ and ring CY₂ may each independentlybe:

i) a first ring, ii) a second ring, iii) a condensed ring in which atleast two first rings are condensed, iv) a condensed ring in which atleast two second rings are condensed, or v) a condensed ring in which atleast one first ring is condensed with at least one second ring,

wherein the first ring may be a cyclopentane group, a cyclopentadienegroup, a furan group, a thiophene group, a pyrrole group, a silolegroup, an indene group, a benzofuran group, a benzothiophene group, anindole group, a benzosilole group, an oxazole group, an isoxazole group,an oxadiazole group, an isoxadiazole group, an oxatriazole group, anisoxatriazole group, a thiazole group, an isothiazole group, athiadiazole group, an isothiadiazole group, a thiatriazole group, anisothiatriazole group, a pyrazole group, an imidazole group, a triazolegroup, a tetrazole group, an azasilole group, a diazasilole group, or atriazasilole group, and

wherein the second ring may be an adamantane group, a norbornane group,a norbornene group, a cyclohexane group, a cyclohexene group, a phenylgroup, a pyridine group, a pyrimidine group, a pyrazine group, apyridazine group, or a triazine group.

In one or more embodiments, ring CY₁ and ring CY₂ may each independentlybe a cyclopentane group, a cyclohexane group, a cycloheptane group, acyclopentene group, a cyclohexene group, a cycloheptene group, a phenylgroup, a naphthalene group, an anthracene group, a phenanthrene group, atriphenylene group, a pyrene group, a chrysene group, a cyclopentadienegroup, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furangroup, an indole group, a benzoborole group, a benzophosphole group, anindene group, a benzosilole group, a benzogermole group, abenzothiophene group, a benzoselenophene group, a benzofuran group, acarbazole group, a dibenzoborole group, a dibenzophosphole group, afluorene group, a dibenzosilole group, a dibenzogermole group, adibenzothiophene group, a dibenzoselenophene group, a dibenzofurangroup, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, adibenzothiophene 5,5-dioxide group, an azaindole group, anazabenzoborole group, an azabenzophosphole group, an azaindene group, anazabenzosilole group, an azabenzogermole group, an azabenzothiophenegroup, an azabenzoselenophene group, an azabenzofuran group, anazacarbazole group, an azadibenzoborole group, an azadibenzophospholegroup, an azafluorene group, an azadibenzosilole group, anazadibenzogermole group, an azadibenzothiophene group, anazadibenzoselenophene group, an azadibenzofuran group, anazadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, anazadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidinegroup, a pyrazine group, a pyridazine group, a triazine group, aquinoline group, an isoquinoline group, a quinoxaline group, aquinazoline group, a phenanthroline group, a pyrrole group, a pyrazolegroup, an imidazole group, a triazole group, an oxazole group, anisoxazole group, a thiazole group, an isothiazole group, an oxadiazolegroup, a thiadiazole group, a benzopyrazole group, a benzimidazolegroup, a benzoxazole group, a benzothiazole group, a benzoxadiazolegroup, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group,or a 5,6,7,8-tetrahydroquinoline group.

In one or more embodiments, ring CY₁ and ring CY₂ may each independentlybe a phenyl group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalenegroup, a phenanthrene group, a pyridine group, a pyrimidine group, apyrazine group, a triazine group, a quinoline group, an isoquinolinegroup, a quinoxaline group, a quinazoline group, a phenanthroline group,a benzofuran group, a benzothiophene group, a fluorene group, acarbazole group, a dibenzofuran group, a dibenzothiophene group, adibenzosilole group, an azafluorene group, an azacarbazole group, anazadibenzofuran group, an azadibenzothiophene group, or anazadibenzosilole group.

In one or more embodiments, ring CY₁ may be a pyridine group, apyrimidine group, a pyrazine group, a triazine group, a quinoline group,an isoquinoline group, a quinoxaline group, or a quinazoline group.

In one or more embodiments, ring CY₂ may be a phenyl group, anaphthalene group, a pyridine group, a pyrimidine group, a pyrazinegroup, a triazine group, a quinoline group, an isoquinoline group, aquinoxaline group, a quinazoline group, a fluorene group, a carbazolegroup, a dibenzofuran group, a dibenzothiophene group, or adibenzosilole group.

In one or more embodiments, Ln₁ may be represented by Formula 1A-1 or1A-2:

wherein, in Formulae 1A-1 and 1A-2,

Y₁ may be O, S, Se, or C(R_(29A))(R_(29B)),

X₁₁ may be C(R₁₁) or N, X₁₂ may be C(R₁₂) or N, X₁₃ may be C(R₁₃) or N,and X₁₄ may be C(R₁₄) or N,

X₂₁ may be C(R₂₁) or N, X₂₂ may be C(R₂₂) or N, X₂₃ may be C(R₂₃) or N,and X₂₄ may be C(R₂₄) or N,

X₂₅ may be C(R₂₅) or N, X₂₆ may be C(R₂₅) or N, X₂₇ may be C(R₂₇) or N,and X₂₈ may be C(R₂₈) or N,

R₁₁ to R₁₄ are each independently as described in connection with R₁₀,

R₂₁ to R₂₈, R_(29A), and R_(29B) are each independently as described inconnection with R₂₀, and

* and *¹ each indicate a binding site to M₁.

In one or more embodiments, Y₁ may be O or S.

Ln₂ in Formula 1 is a ligand represented by Formula 1B.

Ring CY₃ in Formula 1B is a 6-membered heterocyclic group; a 6-memberedheterocyclic group condensed with a C₅-C₃₀ carbocyclic group, or a6-membered heterocyclic group condensed with a C₁-C₃₀ heterocyclicgroup.

In one or more embodiments, ring CY₃ may be a pyridine group, apyrimidine group, a pyrazine group, a pyridazine group, a triazinegroup, a quinoline group, an isoquinoline group, a benzoquinoline group,a benzoisoquinoline group, a phenanthroline group, a quinoxaline group,or a quinazoline group.

Ring CY₄ in Formula 1B is a 6-membered carbocyclic group; a 6-memberedheterocyclic group; a 6-membered carbocyclic group condensed with aC₅-C₃₀ carbocyclic group or a C₁-C₃₀ heterocyclic group; a 6-memberedcarbocyclic group condensed with a C₅-C₃₀ carbocyclic group; a6-membered heterocyclic group condensed with a C₅-C₃₀ carbocyclic group;or a 6-membered heterocyclic group condensed with a C₁-C₃₀ heterocyclicgroup.

In one or more embodiments, ring CY₄ may be a phenyl group, anaphthalene group, a pyridine group, a pyrimidine group, a pyrazinegroup, a pyridazine group, a triazine group, a quinoline group, anisoquinoline group, a benzoquinoline group, a benzoisoquinoline group, aphenanthroline group, a quinoxaline group, or a quinazoline group.

Y₂ in Formula 1B is O or S.

In one or more embodiments, Y2 may be O.

In one or more embodiments, Ln₂ may be represented by Formula 1B-1:

wherein, in Formula 1B-1,

X₃₁ may be C(R₃₁) or N, X₃₂ may be C(R₃₂) or N, X₃₃ may be C(R₃₃) or N,and X₃₄ may be C(R₃₄) or N,

X₄₁ may be C(R₄₁) or N, X₄₂ may be C(R₄₂) or N, X₄₃ may be C(R₄₃) or N,and X₄₄ may be C(R₄₄) or N,

R₃₁ to R₃₄ are each independently as described in connection with R₃₀,

R₄₁ to R₄₄ are each independently as described in connection with R₄₀,and

* and *′ each indicate a binding site to M₁.

R₁₀, R₂₀, R₃₀, and R₄₀ in Formulae 1A and 1B are each independentlyhydrogen, deuterium, —F, —Cl, —Br, —I, SF₅, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an am idino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₁-C₆₀ alkylthiogroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₇-C₆₀alkyl aryl group, a substituted or unsubstituted C₇-C₆₀ aryl alkylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₂-C₆₀ alkyl heteroaryl group, a substituted or unsubstituted C₂-C₆₀heteroaryl alkyl group, a substituted or unsubstituted C₁-C₆₀heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —Ge(Q₁)(Q₂)(Q₃), —N(Q₄)(Q₅), —B(Q₈)(Q₇), —P(Qs)(Q₉), or—P(=O)(Qs)(Q₉).

b10, b20, b30, and b40 in Formulae 1A and 1B are each independently 1,2, 3, 4, 5, 6, 7, 8, 9, or 10.

In one or more embodiments, b10, b20, b30, and b40 may eachindependently be 1, 2, 3, 4, 5, 6, 7, or 8.

In one or more embodiments, b10, b20, b30, and b40 may eachindependently be 1, 2, 3, 4, 5, or 6.

In one or more embodiments, b10, b20, b30, and b40 may eachindependently be 1, 2, 3, or 4.

In one or more embodiments, b10, b20, b30, and b40 may eachindependently be 1 or 2.

In one or more embodiments, R₁₀, R₂₀, R₃₀, and R₄₀ may eachindependently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3,—CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, or a C₁-C₂₀ alkylthio group;

a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, or a C₁-C₂₀ alkylthiogroup, each substituted with at least one of deuterium, —F, —Cl, —Br,—I, —SF5, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF2H, —CFH2, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₁₀ alkyl group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinylgroup;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl, group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenyl group, a pyrenyl group, a chrysenyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adivenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, or an imidazopyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cyclohepyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group,acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthrocenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, or an imidazopyrimidinyl group, eachsubstituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF₅,—CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group,a nitro group, an amino group, an am idino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkylthio group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctylgroup, an adamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, an imidazopyrimidinyl group, or a combination thereof; or

—Si(Q₁)(Q₂)(Q₃), —Ge(Q₁)(Q₂)(Q₃), —N(Q₄)(Q₅), —B(Q₆)(Q₇), —P(Q₈)(Q₉), or—P(═O)(Q₈)(Q₉).

In one or more embodiments, R₁₀, R₂₀, R₃₀, and R₄₀ may eachindependently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, —CD₃, —CD₂H, —CDH₂, —CF₃,—CF₂H, —CFH2, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, or a C₁-C₆₀ alkylthio group; or

a group represented by one of Formulae 9-1 to 9-67, 9-201 to 9-244, 10-1to 10-154, or 10-201 to 10-350:

wherein, in Formulae 9-1 to 9-67, 9-201 to 9-244, 10-1 to 10-154, and10-201 to 10-350, * indicates a binding site to a neighboring atom, “Ph”is a phenyl group, “TMS” is a trimethylsilyl group, and “TMG” is atrimethylgermyl group.

In Formulae 1A and 1B, neighboring two or more of a plurality of Rio areoptionally bonded together to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclicgroup; neighboring two or more of a plurality of R₂₀ are optionallybonded together to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclicgroup; neighboring two or more of a plurality of R₃₀ are optionallybonded together to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclicgroup; neighboring two or more of a plurality of R₄₀ are optionallybonded together to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclicgroup; and neighboring two or more of R₁₀, R₂₀, R₃₀, and R₄₀ areoptionally bonded together to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclicgroup.

In one or more embodiments, two or more of a plurality of Rio; two ormore of a plurality of R₂₀; two or more of a plurality of R₃₀; two ormore of a plurality of R₄₀, neighboring two or more of R₁₀, R₂₀, R₃₀,and R₄₀ may optionally be bonded together via a single bond, a doublebond, or a first linking group to form a C₅-C₃₀ carbocyclic groupunsubstituted or substituted with at least one R_(10a) or a C₁-C₃₀heterocyclic group unsubstituted or substituted with at least oneR_(10a) (for example, a fluorene group, a xanthene group, or an acridinegroup, each unsubstituted or substituted with at least one R_(10a)).R_(10a) is as described in connection with R₁₀.

The first linking group may be *—N(R₈)—*′, *—B(R₈)—*′, *—P(R₈)—*′,*—C(R₈)(R₉)—*′, *—Si(R₈)(R₉)—*′, *—Ge(R₈)(R₉)—*′, *—Se—', *—C(═O)—*',*—S(═O)—*′, ^(*—)S(═O)₂—*′, *—C(R₈)=*′, *═C(R₈)—*′, *—C(R₈)=C(R₉)—*′,*—C(═S)—*′, and *—C≡C—*′, wherein R₈ and R₉ are each as described inconnection with R₁₀, and * and *′ each indicate a binding site to aneighboring atom.

In one or more embodiments, Q₁to Q₉, Q₁₁ to Q₁₉, Q₂₁ to Q₂₉, and Q₃₁ toQ₃₉ may each independently be:

deuterium, —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H,—CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, or—CD₂CDH₂;

an n-propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, or a naphthyl group; or

an n-propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, or a naphthyl group, each substituted with at least one ofdeuterium, a C₁-C₁₀ alkyl group, a phenyl group, or a combinationthereof.

In one or more embodiments, the organometallic compound may be acompound represented by one of Formulae 30-1 and 30-2:

wherein, in Formulae 30-1 and 30-2,

M₁, n1, n2, and Y₂ are respectively as those described in the presentspecification,

Y₁ may be O, S, Se, or C(R_(29A))(R_(29B)),

R₁₁ to R₁₄ are each independently as described in connection with R₁₀,

R₂₁ to R₂₈, R_(29A), and R_(29B) are each independently as described inconnection with R₂₀,

R₃₁ to R₃₄ are each independently as described in connection with R₃₀,and

R₄₁ to R₄₄ are each independently as described in connection with R₄₀.

In one or more embodiments, examples of the “C₅-C₃₀ carbocyclic groupunsubstituted or substituted with at least one R_(10a) or a C₁-C₃₀heterocyclic group unsubstituted or substituted with at least oneR_(10a)” include a phenyl group, a naphthalene group, a cyclopentanegroup, a cyclopentadiene group, a cyclohexane group, a cycloheptanegroup, a bicyclo[2.2.1]heptane group, a furan group, a thiophene group,a pyrrole group, a silole group, an indene group, a benzofuran group, abenzothiophene group, an indole group, or a benzosilole group, eachunsubstituted or substituted with at least one R_(10a). R_(10a) is asdescribed in connection with Rio. The C₅-C₃₀ carbocyclic group and theC₁-C₃₀ heterocyclic group are respectively as those described in thepresent specification.

In one or more embodiments, at least one of Rio in the number of b10,R₂₀ in the number of b20, R₃₀ in the number of b30, or R₄₀ in the numberof b40 may be a methyl group, an ethyl group, an n-propyl group, anisopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group,a tert-butyl group, an n-pentyl group, an isopentyl group, a2-methylbutyl group, a sec-pentyl group, a tert-pentyl group, aneo-pentyl group, a 3-pentyl group, a 3-methyl-2-butyl group, acyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclooctyl group, a phenyl group, abiphenyl group, a C₁-C₂₀ alkylphenyl group, a naphthyl group,—Si(Q₁)(Q₂)(Q₃), or —Ge(Q₁)(Q₂)(Q₃), each unsubstituted or substitutedwith at least one deuterium.

In one or more embodiments, at least one of R₁₀, R₂₀, R₃₀, and R₄₀ maybe a methyl group, an ethyl group, an n-propyl group, an isopropylgroup, an n-butyl group, an isobutyl group, a sec-butyl group, atert-butyl group, an n-pentyl group, an isopentyl group, a 2-methylbutylgroup, a sec-pentyl group, a tert-pentyl group, a neo-pentyl group, a3-pentyl group, a 3-methyl-2-butyl group, a cyclopentyl group, or acyclohexyl group.

In one or more embodiments, the organometallic compound may be one ofCompounds 1 to 30:

In one or more embodiments, the organometallic compound may beelectrically neutral.

The organometallic compound represented by Formula 1 satisfies thestructure of Formula 1 described above, and includes the ligandsrepresented by Formulae 1A and 1B. In the ligand represented by Formula1B, ring CY₃ including a 6-membered heterocyclic group is linked to ringCY₄ including a 6-membered carbocyclic group or a 6-memberedheterocyclic group, and ring CY₄ is bonded to metal M₁ via linking groupY₂. Without wishing to be bound to theory, due to this structure, theorganometallic compound represented by Formula 1 has excellentluminescence characteristics and has such characteristics suitable foruse as a luminescent material with high color purity by controlling theemission wavelength range.

In addition, the organometallic compound represented by Formula 1 hasexcellent electrical mobility, and thus, electronic devices includingthe organometallic compound, for example, organic light-emitting devicesincluding the organometallic compound may show a low driving voltage,high efficiency, a long lifespan, and a reduced roll-off phenomenon.

In addition, the photochemical stability of the organometallic compoundrepresented by Formula 1 is improved, and thus, electronic devicesincluding the organometallic compound, for example, organiclight-emitting devices including the organometallic compound may showhigh luminescence efficiency, a long lifespan, and high color purity.

A highest occupied molecular orbital (HOMO) energy level, a lowestunoccupied molecular orbital (LUMO) energy level, a singlet (S₁) energylevel, and a triplet (T₁) energy level of organometallic compoundrepresented by Formula 1 were evaluated by density functional theory(DFT) using the Gaussian 09 program with the molecular structureoptimization obtained at the B3LYP level, and results thereof are shownin Table 1, where the energy levels are reported as electron Volts (eV).

TABLE 1 HOMO LUMO S₁ T₁ Compound (eV) (eV) (eV) (eV) Compound 1 −4.546−1.242 2.640 2.444 Compound 4 −4.620 −1.375 2.600 2.373

From Table 1, it is confirmed that the organometallic compoundrepresented by Formula 1 has such electric characteristics that aresuitable for use as a dopant for an electronic device, for example, anorganic light-emitting device.

In one or more embodiments, a full width at half maximum (FWHM) of anemission peak of an emission spectrum or an electroluminescence (EL)spectrum of the organometallic compound may be about 70 nm or less. Forexample, the FWHM of the emission peak of the emission spectrum or theEL spectrum of the organometallic compound may be in a range of about 30nm to about 65 nm, about 40 nm to about 63 nm, or about 45 nm to about62 nm.

In one or more embodiments, a maximum emission wavelength (emission peakwavelength maximum, λ_(max)) of the emission peak of the emissionspectrum or the EL spectrum of the organometallic compound may be in arange of about 490 nm to about 550 nm.

Synthesis methods of the organometallic compound represented by Formula1 may be recognizable by one of ordinary skill in the art and byreferring to Synthesis Examples provided below.

The organometallic compound represented by Formula 1 is suitable for usein an organic layer of an organic light-emitting device, for example,for use as a dopant in an emission layer of the organic layer. Thus,another aspect provides an organic light-emitting device that includes:a first electrode; a second electrode; and an organic layer that islocated between the first electrode and the second electrode andincludes an emission layer, wherein the organic layer includes at leastone of the organometallic compound represented by Formula 1.

As described above, due to the inclusion of the organic layer includingthe organometallic compound represented by Formula 1, the organiclight-emitting device may have excellent characteristics in terms ofdriving voltage, current efficiency, power efficiency, external quantumefficiency, lifespan, and/or color purity. Also, such an organiclight-emitting device may have a reduced roll-off phenomenon and arelatively narrow FWHM of an emission peak in an EL spectrum.

The organometallic compound of Formula 1 may be used between a pair ofelectrodes of the organic light-emitting device. For example, theorganometallic compound represented by Formula 1 may be included in theemission layer. In this regard, the organometallic compound may act as adopant, and the emission layer may further include a host (that is, anamount of the organometallic compound represented by Formula 1 in theemission layer is smaller than an amount of the host).

In one or more embodiments, the emission layer may emit green light. Forexample, the emission layer may emit green light having a maximumemission wavelength in a range of about 490 nm to about 550 nm.

The expression “(an organic layer) includes at least one oforganometallic compounds” used herein may include a case in which “(anorganic layer) includes identical organometallic compounds representedby Formula 1” and a case in which “(an organic layer) includes two ormore different organometallic compounds represented by Formula 1.”

For example, the organic layer may include, as the organometalliccompound, only Compound 1. In this regard, Compound 1 may be included inthe emission layer of the organic light-emitting device. In one or moreembodiments, the organic layer may include, as the organometalliccompound, Compound 1 and Compound 2. In this regard, Compound 1 andCompound 2 may be present in an identical layer (for example, bothCompound 1 and Compound 2 may be present in the emission layer).

The first electrode may be an anode, which is a hole injectionelectrode, and the second electrode may be a cathode, which is anelectron injection electrode. Alternatively, the first electrode may bea cathode, which is an electron injection electrode, and the secondelectrode may be an anode, which is a hole injection electrode.

For example, in the organic light-emitting device, the first electrodemay be an anode, the second electrode may be a cathode, and the organiclayer may further include a hole transport region located between thefirst electrode and the emission layer and an electron transport regionlocated between the emission layer and the second electrode, wherein thehole transport region may include a hole injection layer, a holetransport layer, an electron blocking layer, a buffer layer, or acombination thereof, and the electron transport region may include ahole blocking layer, an electron transport layer, an electron injectionlayer, or a combination thereof.

The term “organic layer” as used herein refers to a single layer and/ora plurality of layers located between the first electrode and the secondelectrode of the organic light-emitting device. The “organic layer” mayinclude, in addition to an organic compound, an organometallic complexincluding metal.

The FIGURE is a schematic cross-sectional view of an organiclight-emitting device 10 according to one or more embodiments.Hereinafter, the structure and manufacturing method of the organiclight-emitting device 10 according to one or more embodiments will bedescribed in further detail with reference to the FIGURE. In the FIGURE,the organic light-emitting device 10 includes a first electrode 11, anorganic layer 15, and a second electrode 19, which are sequentiallystacked.

A substrate may be additionally located under the first electrode 11 oron the second electrode 19. For use as the substrate, any substrate thatis used in organic light-emitting devices available in the art may beused, and the substrate may be a glass substrate or a transparentplastic substrate, each having excellent mechanical strength, thermalstability, transparency, surface smoothness, ease of handling, and/orwater resistance.

The first electrode 11 may be, for example, formed by depositing orsputtering a material for forming the first electrode 11 on thesubstrate. The first electrode 11 may be an anode. The material forforming the first electrode 11 may be selected from materials with ahigh work function to facilitate hole injection. The first electrode 11may be a reflective electrode, a semi-transmissive electrode, or atransmissive electrode. The material for forming the first electrode 11may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide(SnO₂), or zinc oxide (ZnO). In one or more embodiments, the materialfor forming the first electrode 11 may be a metal, such as magnesium(Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al—Li), calcium(Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).

The first electrode 11 may have a single-layered structure or amulti-layered structure including two or more layers. For example, thefirst electrode 11 may have a three-layered structure of ITO/Ag/ITO, butthe structure of the first electrode 11 is not limited thereto.

The organic layer 15 may be located on the first electrode 11.

The organic layer 15 may include a hole transport region, an emissionlayer, and an electron transport region.

The hole transport region may be located between the first electrode 11and the emission layer.

The hole transport region may include a hole injection layer, a holetransport layer, an electron blocking layer, a buffer layer, or acombination thereof.

The hole transport region may include only a hole injection layer oronly a hole transport layer. In one or more embodiments, the holetransport region may have a hole injection layer/hole transport layerstructure, or a hole injection layer/hole transport layer/electronblocking layer structure, wherein, for each structure, respective layersare sequentially stacked in this stated order from the first electrode11.

When the hole transport region includes a hole injection layer, the holeinjection layer may be formed on the first electrode 11 by using one ormore suitable methods, such as vacuum deposition, spin coating, casting,and Langmuir-Blodgett (LB) deposition.

When the hole injection layer is formed by vacuum deposition, thedeposition conditions may vary according to a material that is used toform the hole injection layer, and the structure and thermalcharacteristics of the hole injection layer. For example, the depositionconditions may include a deposition temperature in a range of about 100°C. to about 500° C., a vacuum pressure in a range of about 10⁻⁸ torr toabout 10⁻³ torr, and a deposition rate in a range of about 0.01angstroms per second (Å/sec) to about 100Å/sec. However, the depositionconditions are not limited thereto.

When the hole injection layer is formed by spin coating, the coatingconditions may vary according to a material that is used to form thehole injection layer, and the structure and thermal characteristics ofthe hole injection layer. For example, the coating conditions mayinclude a coating speed in a range of about 2,000 revolutions per minute(rpm) to about 5,000 rpm and a heat treatment temperature for removing asolvent after coating in a range of about 80° C. to about 200° C.However, the coating conditions are not limited thereto.

The conditions for forming the hole transport layer and the electronblocking layer may be similar to or the same as the conditions forforming the hole injection layer.

The hole transport region may include at least one of4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA),4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA),4,4′,4″-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA),N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB), β-NPB,N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine(TPD), spiro-TPD, spiro-NPB, methylated NPB, 4,4′-cyclohexylidenebis[N,N-bis(4-methylphenyl)benzenamine] (TAPC),4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD),4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (PANI/CSA),polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound representedby Formula 201, or a compound represented by Formula 202, butembodiments are not limited thereto:

wherein, in Formula 201, Ar₁₀₁ and Ar₁₀₂ may each independently be:

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anacenaphthylene group, a fluorenylene group, a phenalenylene group, aphenanthrenylene group, an anthracenylene group, a fluoranthenylenegroup, a triphenylenylene group, a pyrenylene group, a chrysenylenylenegroup, a naphthacenylene group, a picenylene group, a perylenylenegroup, or a pentacenylene group; or

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anacenaphthylene group, a fluorenylene group, a phenalenylene group, aphenanthrenylene group, an anthracenylene group, a fluoranthenylenegroup, a triphenylenylene group, a pyrenylene group, a chrysenylenylenegroup, a naphthacenylene group, a picenylene group, a perylenylenegroup, or a pentacenylene group, each substituted with at least one ofdeuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₁-C₆₀ alkylthio group, a C₃-C₁₀ cycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₇-C₆₀ alkylaryl group, a C₇-C₆₀ aryl alkyl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀ heteroaryl group, a C₂-C₆₀ alkyl heteroarylgroup, a C₂-C₆₀ heteroaryl alkyl group, a C₁-C₆₀ heteroaryloxy group, aC₁-C₆₀ heteroarylthio group, a monovalent non-aromatic condensedpolycyclic group, a monovalent non-aromatic condensed heteropolycyclicgroup, or a combination thereof.

xa and xb in Formula 201 may each independently be an integer from 0 to5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0, but xa andxb are not limited thereto.

R₁₀₁ to R₁₀₈, R₁₁₁ to R₁₁₉, and R₁₂₁ to R₁₂₄ in Formulae 201 and 202 mayeach independently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group (for example, a methyl group, an ethylgroup, a propyl group, a butyl group, pentyl group, or a hexyl group), aC₁-C₁₀ alkoxy group (for example, a methoxy group, an ethoxy group, apropoxy group, a butoxy group, or a pentoxy group), or a C₁-C₆₀alkylthio group;

a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, or a C₁-C₁₀ alkylthiogroup, each substituted with at least one of deuterium, —F, —Cl, —Br,—I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, or a combinationthereof;

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, or a pyrenyl group; or

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, or a pyrenyl group, each substituted with at least one ofdeuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a C₁-C₁₀ alkylthio group,or a combination thereof, but embodiments are not limited thereto.

R₁₀₉ in Formula 201 may be:

a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinylgroup; or a phenyl group, a naphthyl group, an anthracenyl group, or apyridinyl group, each substituted with at least one of deuterium, —F,—Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkylthio group, a phenyl group,a naphthyl group, an anthracenyl group, a pyridinyl group, or acombination thereof.

In one or more embodiments, the compound represented by Formula 201 maybe represented by Formula 201A, but embodiments are not limited thereto:

wherein, in Formula 201A, R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉ are respectively asthose described in the present specification.

For example, the compound represented by Formula 201 and the compoundrepresented by Formula 202 may include one or more of Compounds HT1 toHT20, but embodiments are not limited thereto:

A thickness of the hole transport region may be in a range of about 100angstroms (Å) to about 10,000 Å, for example, about 100 Å to about 1,000Å. When the hole transport region includes at least one of a holeinjection layer and a hole transport layer, a thickness of the holeinjection layer may be in a range of about 100 Å to about 10,000 Å, forexample, about 100 Å to about 1,000 Å, and a thickness of the holetransport layer may be in a range of about 50 Å to about 2,000 Å, forexample, about 100 Å to about 1,500 Å. When the thicknesses of the holetransport region, the hole injection layer, and the hole transport layerare within these ranges, satisfactory hole transporting characteristicsmay be obtained without a substantial increase in driving voltage.

The hole transport region may further include, in addition to thematerials as described above, a charge-generation material for improvingconductive properties. The charge-generation material may behomogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant. Thep-dopant may be one of a quinone derivative, a metal oxide, and a cyanogroup-containing compound, but embodiments are not limited thereto. Forexample, non-limiting examples of the p-dopant include a quinonederivative, such as tetracyanoquinodimethane (TCNQ) or2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); ametal oxide, such as a tungsten oxide or a molybdenum oxide; or a cyanogroup-containing compound, such as Compound HT-D1 or Compound F12, butembodiments are not limited thereto:

The hole transport region may further include a buffer layer.

The buffer layer may compensate for an optical resonance distancedepending on a wavelength of light emitted from the emission layer toimprove the efficiency of an organic light-emitting device.

The emission layer may be formed on the hole transport region by usingone or more suitable methods, such as vacuum deposition, spin coating,casting, or LB deposition. When the emission layer is formed by vacuumdeposition or spin coating, the deposition or coating conditions may besimilar to those applied in forming the hole injection layer althoughthe deposition or coating conditions may vary according to a materialthat is used to form the hole transport layer.

Meanwhile, when the hole transport region includes an electron blockinglayer, a material for forming the electron blocking layer may beselected from materials for the hole transport region described aboveand host materials to be described below, but embodiments are notlimited thereto. For example, when the hole transport region includes anelectron blocking layer, the material for forming the electron blockinglayer may be mCP, which will be described below.

The emission layer may include a host and a dopant, and the dopant mayinclude the organometallic compound represented by Formula 1.

The host may include at least one of1,3,5-tri(1-phenyl-1H-benzo[d]imidazol yl)phenyl (TPBi),3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN),9,10-di(naphthalene-2-yl)anthracene (ADN) (also referred to as “DNA”),4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP),4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl (CDBP),1,3,5-tris(carbazole-9-yl)benzene (TCP), 1,3-bis(N-carbazolyl)benzene(mCP), Compound H50, or Compound H51, but embodiments are not limitedthereto:

In one or more embodiments, the host may further include a compoundrepresented by Formula 301:

wherein, in Formula 301, Ar₁₁₁ and Ar₁₁₂ may each independently be:

a phenylene group, a naphthylene group, a phenanthrenylene group, or apyrenylene group; or

a phenylene group, a naphthylene group, a phenanthrenylene group, or apyrenylene group, each substituted with at least one of a phenyl group,a naphthyl group, an anthracenyl group, or a combination thereof.

Ar₁₁₃ to Ar₁₁₆ in Formula 301 may each independently be:

a C₁-C₁₀ alkyl group, a phenyl group, a naphthyl group, a phenanthrenylgroup, or a pyrenyl group; or

a phenyl group, a naphthyl group, a phenanthrenyl group, or a pyrenylgroup, each substituted with at least one of a phenyl group, a naphthylgroup, an anthracenyl group, or a combination thereof.

g, h, i, and j in Formula 301 may each independently be an integer from0 to 4, and for example, may each independently be 0, 1, or 2.

Ar₁₁₃ and Ar₁₁₆ in Formula 301 may each independently be:

a C₁-C₁₀ alkyl group substituted with at least one of a phenyl group, anaphthyl group, an anthracenyl group, or a combination thereof;

a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group,a phenanthrenyl group, or a fluorenyl group;

a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group,a phenanthrenyl group, or a fluorenyl group, each substituted with atleast one of deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, acyano group, a nitro group, an amino group, an am idino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₁-C₂₀ alkylthio group, aphenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, aphenanthrenyl group, a fluorenyl group, or a combination thereof; or agroup represented by formula:

In one or more embodiments, the host may include a compound representedby Formula 302:

wherein, in Formula 302, Ar₁₂₂ to Ar₁₂₅ are each as described inconnection with Ar₁₁₃ in Formula 301.

Ar₁₂₆ and Ar₁₂₇ in Formula 302 may each independently be a C₁-C₁₀ alkylgroup (for example, a methyl group, an ethyl group, or a propyl group).

k and l in Formula 302 may each independently be an integer from 0 to 4.For example, k and l may each independently be 0, 1, or 2.

When the organic light-emitting device 10 is a full-color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, and a blue emission layer. Inone or more embodiments, due to a stacked structure including a redemission layer, a green emission layer, and/or a blue emission layer,the emission layer may emit white light.

When the emission layer includes a host and a dopant, an amount of thedopant may be in a range of about 0.01 part by weight to about 15 partsby weight based on 100 parts by weight of the host, but embodiments arenot limited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within these ranges, excellentlight-emission characteristics may be obtained without a substantialincrease in driving voltage.

Next, the electron transport region may be located on the emissionlayer.

The electron transport region may include a hole blocking layer, anelectron transport layer, an electron injection layer, or a combinationthereof.

For example, the electron transport region may have a hole blockinglayer/electron transport layer/electron injection layer structure, or anelectron transport layer/electron injection layer structure, butembodiments are not limited thereto. The electron transport layer mayhave a single-layered structure or a multi-layered structure includingtwo or more different materials.

Conditions for forming the hole blocking layer, the electron transportlayer, and the electron injection layer which constitute the electrontransport region may be similar to or the same as the conditions forforming the hole injection layer.

When the electron transport region includes a hole blocking layer, thehole blocking layer may include, for example, at least one of2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP),4,7-diphenyl-1,10-phenanthroline (Bphen), orbis(2-methyl-8-quinolinolato-N1,08)-(1,1′-biphenyl-4-olato)aluminum(BAlq), but embodiments are not limited thereto:

A thickness of the hole blocking layer may be in a range of about 20 Åto about 1,000 Å, for example, about 30 Å to about 300 Å. When thethickness of the hole blocking layer is within these ranges, excellenthole blocking characteristics may be obtained without a substantialincrease in driving voltage.

The electron transport layer may further include at least one of BCP,Bphen, tris(8-hydroxy-quinolinato)aluminum (Alq3), BAlq,3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), and4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), butembodiments are not limited thereto:

In one or more embodiments, the electron transport layer may include atleast one of Compounds ET1 to ET25, but embodiments are not limitedthereto:

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. When thethickness of the electron transport layer is within these ranges,satisfactory electron transporting characteristics may be obtainedwithout a substantial increase in driving voltage.

The electron transport layer may include, in addition to the materialsdescribed above, a metal-containing material.

The metal-containing material may include a Li complex. The Li complexmay include, for example, Compound ET-D1 (lithium quinolate (LiQ)) orET-D2:

The electron transport region may include an electron injection layerthat facilitates electron injection from the second electrode 19.

The electron injection layer may include LiF, NaCl, CsF, Li₂O, BaO, or acombination thereof.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, and, for example, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within these ranges,satisfactory electron injection characteristics may be obtained withouta substantial increase in driving voltage.

The second electrode 19 is located on the organic layer 15. The secondelectrode 19 may be a cathode. A material for forming the secondelectrode 19 may be a metal, an alloy, an electrically conductivecompound, or a combination thereof, which has a relatively low workfunction. For example, the material for forming the second electrode 19may be lithium (Li), magnesium (Mg), aluminum (Al), silver (Ag),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), ormagnesium-silver (Mg—Ag). In one or more embodiments, to manufacture atop-emission type light-emitting device, a transmissive electrode formedusing ITO or IZO may be used as the second electrode 19.

Hereinbefore, the organic light-emitting device 10 has been describedwith reference to the FIGURE, but embodiments are not limited thereto.

Another aspect provides a diagnostic composition including at least oneof the organometallic compound represented by Formula 1.

Since the organometallic compound represented by Formula 1 provides highluminescence efficiency, the diagnostic composition including theorganometallic compound may have high diagnostic efficiency.

The diagnostic composition may be used in various applications includinga diagnosis kit, a diagnosis reagent, a biosensor, a biomarker, and thelike.

The term “C₁-C₆₀ alkyl group” as used herein refers to a linear orbranched saturated aliphatic hydrocarbon monovalent group having 1 to 60carbon atoms, and examples thereof include a methyl group, an ethylgroup, a propyl group, an isobutyl group, a sec-butyl group, atert-butyl group, a pentyl group, an isoamyl group, a hexyl group, andthe like. The term “C₁-C₆₀ alkylene group” as used herein refers to adivalent group having the same structure as the C₁-C₆₀ alkyl group.

The term “C₁-C₆₀ alkoxy group” as used herein refers to a monovalentgroup represented by —OA₁₀₁ (wherein Aioi is the C₁-C₆₀ alkyl group),and examples thereof include a methoxy group, an ethoxy group, anisopropyloxy group, and the like.

The term “C₁-C₆₀ alkylthio group” as used herein refers to a monovalentgroup represented by —SA_(101′), (wherein A_(101′), is the C₁-C₆₀ alkylgroup).

The term “C₂-C₆₀ alkenyl group” as used herein refers to a hydrocarbongroup formed by substituting at least one carbon-carbon double bond inthe middle or at the terminus of the C₂-C₆₀ alkyl group, and examplesthereof include an ethenyl group, a propenyl group, a butenyl group, andthe like. The term “C₂-C₆₀ alkenylene group” as used herein refers to adivalent group having the same structure as the C₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group” as used herein refers to a hydrocarbongroup formed by substituting at least one carbon-carbon triple bond inthe middle or at the terminus of the C₂-C₆₀ alkyl group, and examplesthereof include an ethynyl group, a propynyl group, and the like. Theterm “C₂-C₆₀ alkynylene group” as used herein refers to a divalent grouphaving the same structure as the C₂-C₆₀ alkynyl group.

The term “C₃-C₁₀ cycloalkyl group” as used herein refers to a monovalentsaturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, andexamples thereof include a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, and thelike. The term “C₃-C₁₀ cycloalkylene group” as used herein refers to adivalent group having the same structure as the C₃-C₁₀ cycloalkyl group.

The term “C₁-C₁₀ heterocycloalkyl group” as used herein refers to amonovalent saturated monocyclic group having at least one heteroatomselected from N, O, P, Si, Ge, Se, and S as a ring-forming atom and 1 to10 carbon atoms, and examples thereof include a tetrahydrofuranyl group,a tetrahydrothiophenyl group, and the like. The term “C₁-C₁₀heterocycloalkylene group” as used herein refers to a divalent grouphaving the same structure as the C₁-C₁₀ heterocycloalkyl group.

The term “C₃-C₁₀ cycloalkenyl group” as used herein refers to amonovalent monocyclic group that has 3 to 10 carbon atoms and at leastone carbon-carbon double bond in the ring thereof and no aromaticity,and examples thereof include a cyclopentenyl group, a cyclohexenylgroup, a cycloheptenyl group, and the like. The term “C₃-C₁₀cycloalkenylene group” as used herein refers to a divalent group havingthe same structure as the C₃-C₁₀ cycloalkenyl group.

The term “C₂-C₁₀ heterocycloalkenyl group” as used herein refers to amonovalent monocyclic group that has at least one heteroatom selectedfrom N, O, P, Si, Ge, Se, and S as a ring-forming atom, 2 to 10 carbonatoms as ring-forming atoms, and at least one carbon-carbon double bondin its ring. Examples of the C₁-C₁₀ heterocycloalkenyl group include a2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like.The term “C₂-C₁₀ heterocycloalkenylene group” as used herein refers to adivalent group having the same structure as the C₂-C₁₀heterocycloalkenyl group.

The term “C₆-C₆₀ aryl group” as used herein refers to a monovalent grouphaving a carbocyclic aromatic system having 6 to 60 carbon atoms, andthe term “C₆-C₆₀ arylene group” as used herein refers to a divalentgroup having a carbocyclic aromatic system having 6 to 60 carbon atoms.Examples of the C₆-C₆₀ aryl group include a phenyl group, a naphthylgroup, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, achrysenyl group, and the like. When the C₆-C₆₀ aryl group and the C₆-C₆₀arylene group each include two or more rings, the two or more rings maybe fused to each other.

The term “C₇-C₆₀ alkyl aryl group” as used herein refers to a C₆-C₆₀aryl group substituted with at least one C₁-C₆₀ alkyl group. The term“C₇-C₆₀ aryl alkyl group” as used herein refers to a C₁-C₆₀ alkyl groupsubstituted with at least one C₆-C₆₀ aryl group.

The term “C₁-C₆₀ heteroaryl group” as used herein refers to a monovalentgroup having a cyclic aromatic system that has at least one heteroatomselected from N, O, P, Si, Ge, Se, and S as a ring-forming atom, and 1to 60 carbon atoms. The term “C₁-C₆₀ heteroarylene group” as used hereinrefers to a divalent group having a carbocyclic aromatic system that hasat least one heteroatom selected from N, O, P, Si, Ge, Se, and S as aring-forming atom, and 1 to 60 carbon atoms. Examples of the C₁-C₆₀heteroaryl group include a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, an isoquinolinyl group, and the like. When the C₆-C₆₀ heteroarylgroup and the C₆-C₆₀ heteroarylene group each include two or more rings,the two or more rings may be fused to each other.

The term “C₂-C₆₀ alkyl heteroaryl group” as used herein refers to aC₁-C₆₀ heteroaryl group substituted with at least one C₁-C₆₀ alkylgroup. The term “C₂-C₆₀ heteroaryl alkyl group” as used herein refers toa C₁-C₆₀ heteroaryl group substituted with at least one C₁-C₆₀ alkylgroup.

The term “C₆-C₆₀ aryloxy group” as used herein refers to —OA₁₀₂ (whereinAloe is the C₆-C₆₀ aryl group), and the term “C₆-C₆₀ arylthio group” asused herein refers to —SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group).

The term “C₁-C₆₀ heteroaryloxy group” as used herein refers to —OA₁₀₄(wherein A₁₀₄ is the C₁-C₆₀ heteroaryl group), and the term “C₁-C₆₀heteroarylthio group” as used herein refers to —SA₁₀₅ (wherein A₁₀₅ isthe C₁-C₆₀ heteroaryl group).

The term “monovalent non-aromatic condensed polycyclic group” as usedherein refers to a monovalent group (for example, having 8 to 60 carbonatoms) having two or more rings condensed to each other, only carbonatoms as ring-forming atoms, and no aromaticity in its entire molecularstructure. Examples of the monovalent non-aromatic condensed polycyclicgroup include a fluorenyl group and the like. The term “divalentnon-aromatic condensed polycyclic group” as used herein refers to adivalent group having the same structure as the monovalent non-aromaticcondensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” asused herein refers to a monovalent group (for example, having 2 to 60carbon atoms) having two or more rings condensed with each other, aheteroatom selected from N, O, P, Si, Ge, Se, and S as a ring-formingatom other than carbon atoms, and no aromaticity in its entire molecularstructure. Examples of the monovalent non-aromatic condensedheteropolycyclic group include a carbazolyl group and the like. The term“divalent non-aromatic condensed heteropolycyclic group” as used hereinrefers to a divalent group having the same structure as the monovalentnon-aromatic condensed heteropolycyclic group.

The term “C₅-C₃₀ carbocyclic group” as used herein refers to a saturatedor unsaturated cyclic group including 5 to 30 carbon atoms only asring-forming atoms. The C₅-C₃₀ carbocyclic group may be a monocyclicgroup or a polycyclic group.

The term “C₁-C₃₀ heterocyclic group” as used herein refers to asaturated or unsaturated cyclic group including 1 to 30 carbon atoms andat least one heteroatom selected from N, O, P, Si, Ge, Se, and S asring-forming atoms. The C₁-C₃₀ heterocyclic group may be a monocyclicgroup or a polycyclic group.

The term “TMS” as used herein represents *—Si(CH₃)₃ (trimethylsilyl),and the term “TMG” as used herein represents *—Ge(CH₃)₃(trimethylgermyl).

At least one substituent of the substituted C₅-C₃₀ carbocyclic group,the substituted C₁-C₃₀ heterocyclic group, the substituted C₁-C₆₀ alkylgroup, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substitutedC₁-C₆₀ alkylthio group, the substituted C₃-C₁₀ cycloalkyl group, thesubstituted C₁-C₁₀ heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenyl group, thesubstituted C₆-C₆₀ aryl group, the substituted C₇-C₆₀ alkyl aryl group,the substituted C₇-C₆₀ aryl alkyl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted C₂-C₆₀ alkyl heteroaryl group, thesubstituted C₂-C₆₀ heteroaryl alkyl group, the substituted C₁-C₆₀heteroaryloxy group, the substituted C₁-C₆₀ heteroarylthio group, thesubstituted monovalent non-aromatic condensed polycyclic group, and thesubstituted monovalent non-aromatic condensed heteropolycyclic group maybe:

deuterium, —F, —Cl, —Br, —I, —SF₅, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H,—CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, or aC₁-C₆₀ alkylthio group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, ora C₁-C₆₀ alkoxy group, or a C₁-C₆₀ alkylthio group, each substitutedwith at least one of deuterium, —F, —Cl, —Br, —I, —SF₅, —CD₃, —CD₂H,—CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₇-C₆₀alkyl aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a C₂-C₆₀ alkyl heteroaryl group, a C₁-C₆₀heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —Si(Qi₁)(Q₁₂)(Q₁₃),—Ge(C₂₁₁)(Q₁₂)(Q₁₃), —N(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), —P(Q₁₈)(Q₁₉),—P(═O)(Q₁₈)(Q₁₉), or a combination thereof;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₇-C₆₀ alkyl aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀ heteroaryl group, a C₂-C₆₀ alkyl heteroarylgroup, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, amonovalent non-aromatic condensed polycyclic group, or a monovalentnon-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₇-C₆₀ alkyl aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀ heteroaryl group, a C₂-C₆₀ alkyl heteroarylgroup, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, amonovalent non-aromatic condensed polycyclic group, or a monovalentnon-aromatic condensed heteropolycyclic group, each substituted with atleast one of deuterium, —F, —Cl, —Br, —I, —SF₅, —CD₃, —CD₂H, —CDH₂,—CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxygroup, a C₁-C₆₀ alkylthio group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₇-C₆₀ alkyl arylgroup, a C₇-C₆₀ aryl alkyl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀ heteroaryl group, a C₂-C₆₀ alkyl heteroarylgroup, a C₂-C₆₀ heteroaryl alkyl group, a C₁-C₆₀ heteroaryloxy group, aC₁-C₆₀ heteroarylthio group, a monovalent non-aromatic condensedpolycyclic group, a monovalent non-aromatic condensed heteropolycyclicgroup, —Si(Q₂₁)(Q₂₂)(Q₂₃), —Ge(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₄)(Q₂₅),—B(Q₂₆)(Q₂₇), —P(Q₂₈)(Q₂₉), —P(=O)(Q₂₈)(Q₂₉), or a combination thereof;or

—Si(Q₃₁)(Q₃₂)(Q₃₃), —Ge(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇),—P(Q₃₈)(Q₃₉), or —P(=O)(Q₃₈)(Q₃₉), and

Q₁ to Q₉, Q₁₁ to Q₁₉, Q₂₁ to Q₂₉, and Q₃₁ to Q₃₉ may each independentlybe hydrogen, deuterium, —F, —Cl, —Br, —SF₅, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₁-C₆₀ alkylthiogroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted heterocycloalkenyl group, a substituted or unsubstitutedC₆-C₆₀ aryl group, a substituted or unsubstituted C₇-C₆₀ alkyl arylgroup, a substituted or unsubstituted C₇-C₆₀ aryl alkyl group, asubstituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted orunsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstitutedC₁-C₆₀ heteroaryl group, a substituted or unsubstituted C₂-C₆₀ alkylheteroaryl group, a substituted or unsubstituted C₂-C₆₀ heteroaryl alkylgroup, a C₁-C₆₀ heteroaryloxy group, a CI-Coo heteroarylthio group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, or a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group.

Hereinafter, a compound and an organic light-emitting device accordingto one or more embodiments will be described in detail with reference toSynthesis Examples and Examples, but embodiments are not limitedthereto. The wording 13′ was used instead of ‘A″’ as used in describingSynthesis Examples means that an amount of ‘A’ used was identical to anamount of ‘B’ used, in terms of a molar equivalent.

EXAMPLES Synthesis Example 1 Synthesis of Compound 1

(1) Synthesis of Compound 1A(1)

Under a nitrogen environment, 2-chloro-4-isopropylpyridine (1.5 grams(g), 9.6 millimoles (mmol)) and phenylboronic acid (1.4 g, 11.6 mmol)were dissolved in 180 milliliters (mL) of 1,4-dioxane. Then, potassiumcarbonate (K₂CO₃) (3.1 g, 28.9 mmol) was dissolved in 60 mL of deionized(DI) water and added to the reaction mixture, and a palladium catalyst(tetrakis(triphenylphosphine)palladium(0), Pd(PPh₃)₄) (0.6 g, 0.5 mmol)was added thereto. Afterwards, the resultant reaction mixture wasstirred and heated under reflux at a temperature of 110° C. After anextraction process was performed thereon, a solid thus obtained waspurified by column chromatography (eluent: ethyl acetate (EA) andhexanes) to obtain 1.8 g (yield of 9%) of 4-isopropyl-2-phenylpyridine,which is Compound 1A(1). The obtained compound was identified by highresolution mass spectrometry (HRMS) using matrix assisted laserdesorption ionization (MALDI) and high-performance liquid chromatography(H PLC) analysis.

HRMS (MALDI) calculated for C₁₄H₁₅N: m/z: 197.12 grams per mole (g/mol);found: 197.94 g/mol.

(2) Synthesis of Compound 1A

4-isopropyl-2-phenylpyridine (1.5 g, 7.74 mmol), which is Compound1A(1), and iridium chloride hydrate (1.3 g, 3.69 mmol) were mixed with39 mL of 2-ethoxyethanol and 13 mL of DI water, and then stirred andheated under reflux for 24 hours. Then, the temperature was allowed tolower to room temperature. A solid produced therefrom was separated byfiltration, washed sufficiently with DI water, methanol, and n-hexane,in this stated order, and then dried in a vacuum oven to obtain 2.1 g(yield of 87%) of Compound 1A. Compound 1A obtained was used in the nextreaction without an additional purification process.

(3) Synthesis of Compound 1

Compound 1A (2.0 g, 1.61 mmol), 2-(pyridin-2-yl)phenol (0.55 g, 3.22mmol), and sodium carbonate (Na₂CO₃) (0.51g, 4.84 mmol) were added to areaction vessel, mixed with 30 mL of 2-ethoxyethanol, and then stirredand heated under reflux for 3 hours. Then, the temperature was allowedto lower to room temperature. A solid thus obtained was filtered, washedwith DI water, methanol, and n-hexane, in this stated order, and thendried in a vacuum oven. The obtained solid was purified by columnchromatography (eluent: methylene chloride (MC) and hexanes) to obtain1.42 g (yield of 75%) of Compound 1. The obtained compound wasidentified by HRMS (MALDI) and HPLC analysis.

HRMS (MALDI) calculated for C₃₉H₃₆IrN₃O: m/z: 754.95 g/mol; found:755.79 g/mol.

Synthesis Example 2 Synthesis of Compound 2

1.0 g (yield of 81%) of Compound 2 was obtained in a similar manner asused to synthesize Compound 1, except that [1,1′-biphenyl]-3-ylboronicacid (2.3 g, 11.57 mmol) was used instead of phenylboronic acid insynthesizing Compound 2A(1), and 2-(4-isopropylpyridin-2-yl)phenol (0.55g, 2.59 mmol) was used instead of 2-(pyridin-2-yl)phenol in synthesizingCompound 2. The obtained compound was identified by HRMS (MALDI) andHPLC analysis.

HRMS (MALDI) calculated for C₅₄H₅₀IrN₃O: m/z: 949.23 g/mol; found:950.15 g/mol.

Synthesis Example 3 Synthesis of Compound 4

0.98 g (yield of 84%) of Compound 4 was obtained in a similar manner asused to synthesize Compound 1, except that2-(dibenzo[b,d]furan-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxoborolane (3.4g, 11.57 mmol) was used instead of phenylboronic acid in synthesizingCompound 4A(1). The obtained compound was identified by HRMS (MALDI) andHPLC analysis.

HRMS (MALDI) calculated for C₅₁H₄₀IrN₃O₃: m/z: 935.12 g/mol; found:936.03 g/mol.

Example 1

As an anode, an ITO-patterned glass substrate was cut to a size of 50millimeters (mm)×50 mm×0.5 mm, sonicated with isopropyl alcohol and DIwater, each for 5 minutes, and then cleaned by irradiation ofultraviolet (UV) rays and exposure of ozone for 30 minutes. Theresultant ITO-patterned glass substrate was loaded onto a vacuumdeposition apparatus.

Compounds HT3 and Compound F12 (p-dopant) were co-deposited by vacuum onthe anode at a weight ratio of 98:2 to form a hole injection layerhaving a thickness of 100 Å, and Compound HT3 was vacuum-deposited onthe hole injection layer to form a hole transport layer having athickness of 1,650 Å.

Then, Compound GH3 (host) and Compound 1 (dopant) were co-deposited byvacuum on the hole transport layer at a weight ratio of 92:8 to form anemission layer having a thickness of 400 Å.

Afterwards, Compound ET3 and LiQ (n-dopant) were co-deposited by vacuumon the emission layer at a volume ratio of 50:50 to form an electrontransport layer having a thickness of 350 Å, LiQ (n-dopant) wasvacuum-deposited on the electron transport layer to form an electroninjection layer having a thickness of 10 Å, and Al was vacuum-depositedon the electron injection layer to form a cathode having a thickness of1,000 Å, thereby completing the manufacture of an organic light-emittingdevice.

Example 2 and 3 and Comparative Examples 1 to 3

Organic light-emitting devices were manufactured in a similar manner asin Example 1, except those compounds shown in Table 2 were each usedinstead of Compound 1 as a dopant in forming an emission layer.

The driving voltage, maximum emission wavelength (λ_(max), nm) of theemission spectrum, external quantum efficiency (max EQE, %), androll-off ratio (%) of each of the organic light-emitting devicesmanufactured in Examples 1 and 2 and Comparative Examples 1 to 3 wereevaluated and results thereof are shown in Table 2. As evaluationapparatuses, a current-voltage meter (KEITHLEY 2400) and a luminancemeter (MINOLTA CS-1000A) were used. The roll-off ratio was calculatedaccording to Equation 20 and is a relative value determined based on theinitial or maximum luminescence efficiency.

Roll-off ratio=[1−(efficiency/maximum luminescence efficiency)]×100%  Equation 20

TABLE 2 Dopant in Driving Max Roll- emission voltage EQE off λmax layer(V) (%) (%) (nm) Example 1 Compound 1 4.5 22 12 528 Example 2 Compound 44.5 23 12 536 Example 3 Compound 2 4.5 22 13 532 Comparative Compound A4.7 20 15 528 Example 1 Comparative Compound B 4.8 21 14 538 Example 2Comparative Compound C 4.8 21 16 530 Example 3

Referring to Table 2, it was confirmed that the organic light-emittingdevices of Examples 1 to 3 had low driving voltage and roll-off ratio,and excellent external quantum efficiency. In addition, it was confirmedthat the organic light-emitting devices of Examples 1 to 3 had lowerdriving voltage and roll-off ratio, and higher external quantumefficiency than those of the organic light-emitting devices ofComparative Examples 1 to 3.

As described above, according to the one or more embodiments, anorganometallic compound may have excellent electrical characteristicsand thermal stability. In particular, the organometallic compound mayhave a high glass transition temperature (T_(g)) so that crystallizationthereof may be prevented, and electric mobility thereof may be improved.Accordingly, an electronic device, for example an organic light-emittingdevice, including the organometallic compound may have a low drivingvoltage, a high efficiency, a long lifespan, a reduced roll-off ratio,and a relatively narrow FWHM of an emission peak in an EL spectrum.

Accordingly, by using the organometallic compound, a high-qualityorganic light-emitting device may be implemented. In addition, anelectronic apparatus including the organic light-emitting device may beprovided.

It should be understood that the exemplary embodiments described hereinshould be considered in a descriptive sense and not for purposes oflimitation. Descriptions of features or aspects within each exemplaryembodiment should typically be considered as available for other similarfeatures or aspects in other exemplary embodiments. While one or moreembodiments have been described with reference to the drawing, it willbe understood by those of ordinary skill in the art that various changesin form and details may be made therein without departing from thespirit and scope as defined by the following claims.

What is claimed is:
 1. An organometallic compound represented by Formula1:M₁(Ln₁)_(n1)(Ln₂)n₂   Formula 1 wherein, in Formula 1, M₁ is atransition metal, Ln₁ is a ligand represented by Formula 1A, Ln₂ is aligand represented by Formula 1B, n1 is 1 or 2, and n2 is 1 or 2,

wherein, in Formulae 1A and 1B, ring CY₁ and ring CY₂ are eachindependently a C₅-C₃₀ carbocyclic group or a C₁-C₃₀ heterocyclic group,ring CY₃ is: a 6-membered heterocyclic group; a 6-membered heterocyclicgroup condensed with a C₅-C₃₀ carbocyclic group, or a 6-memberedheterocyclic group condensed with a C₁-C₃₀ heterocyclic group, ring CY₄is: a 6-membered carbocyclic group; a 6-membered heterocyclic group; a6-membered carbocyclic group condensed with a C₅-C₃₀ carbocyclic group ;a 6-membered carbocyclic group condensed with a C₁-C₃₀ heterocyclicgroup; a 6-membered heterocyclic group condensed with a C₅-C₃₀carbocyclic group; or a 6-membered heterocyclic group condensed with aC₁-C₃₀ heterocyclic group, X₁ is C or N, and X₂ is C or N, Y₂ is O or S,R₁₀, R₂₀, R₃₀, and R₄₀ are each independently hydrogen, deuterium, —F,—Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, anamino group, an am idino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₁-C₆₀ alkylthio group, a substituted or unsubstitutedC₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₇-C₆₀ alkyl aryl group, asubstituted or unsubstituted C₇-C₆₀ aryl alkyl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted C₂-C₆₀ alkyl heteroaryl group, asubstituted or unsubstituted C₂-C₆₀ heteroaryl alkyl group, asubstituted or unsubstituted C₁-C₆₀ heteroaryloxy group, a substitutedor unsubstituted C₁-C₆₀ heteroarylthio group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —Ge(Q₁)(Q₂)(Q₃), —N(Q₄)(Q₅),—B(Q₆)(Q₇), —P(Qs)(Q₉), or —P(═O)(Qs)(Q₉), neighboring two or more of aplurality of Rio are optionally bonded together to form a substituted orunsubstituted C₅-C₃₀ carbocyclic group or a substituted or unsubstitutedC₁-C₃₀ heterocyclic group, neighboring two or more of a plurality of R₂₀are optionally bonded together to form a substituted or unsubstitutedC₅-C₃₀ carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, neighboring two or more of a plurality of R₃₀ areoptionally bonded together to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclicgroup, neighboring two or more of a plurality of R₄₀ are optionallybonded together to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclicgroup, P1 neighboring two or more of R₁₀, R₂₀, R₃₀, and R₄₀ areoptionally bonded together to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclicgroup, b10, b20, b30, and b40 are each independently 1, 2, 3, 4, 5, 6,7, 8, 9, or 10, * and *′ each indicate a binding site to M₁, at leastone substituent of the substituted C₅-C₃₀ carbocyclic group, thesubstituted C₁-C₃₀ heterocyclic group, the substituted C₁-C₆₀ alkylgroup, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substitutedC₁-C₆₀ alkylthio group, the substituted C₃-C₁₀ cycloalkyl group, thesubstituted C₁-C₁₀ heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenyl group, thesubstituted C₆-C₆₀ aryl group, the substituted C₇-C₆₀ alkyl aryl group,the substituted C₇-C₆₀ aryl alkyl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted C₂-C₆₀ alkyl heteroaryl group, thesubstituted C₂-C₆₀ heteroaryl alkyl group, the substituted C₁-C₆₀heteroaryloxy group, the substituted C₁-C₆₀ heteroarylthio group, thesubstituted monovalent non-aromatic condensed polycyclic group, and thesubstituted monovalent non-aromatic condensed heteropolycyclic group is:deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H,—CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group,an am idino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, or aC₁-C₆₀ alkylthio group; a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, or a C₁-C₆₀ alkylthiogroup, each substituted with at least one of deuterium, —F, —Cl, —Br,—I, —SF₅, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₇-C₆₀ alkyl arylgroup, a C₇-C₆₀ aryl alkyl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀ heteroaryl group, a C₂-C₆₀ alkyl heteroarylgroup, a C₂-C₆₀ heteroaryl alkyl group, a C₁-C₆₀ heteroaryloxy group, aC₁-C₆₀ heteroarylthio group, a monovalent non-aromatic condensedpolycyclic group, a monovalent non-aromatic condensed heteropolycyclicgroup, —Si(C211)(Q₁₂)(Q₁₃), —Ge(Qii)(Q₁₂)(Q₁₃), —N(Q₁₄)(Q₁₅),—B(Q₁₆)(Q₁₇), —P(Q₁₈)(Q₁₉), —P(═O)(Q₁₈)(Q₁₉), or a combination thereof;a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₇-C₆₀ alkyl aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀ heteroaryl group, a C₂-C₆₀ alkyl heteroarylgroup, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, amonovalent non-aromatic condensed polycyclic group, or a monovalentnon-aromatic condensed heteropolycyclic group; a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₇-C₆₀ alkylaryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a C₂-C₆₀ alkyl heteroaryl group, a C₁-C₆₀heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, a monovalentnon-aromatic condensed polycyclic group, or a monovalent non-aromaticcondensed heteropolycyclic group, each substituted with at least one ofdeuterium, —F, —Cl, —Br, —I, —SF₅, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H,—CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₁-C₆₀alkylthio group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₇-C₆₀ alkyl aryl group, a C₇-C₆₀ aryl alkyl group,a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroarylgroup, a C₂-C₆₀ alkyl heteroaryl group, a C₂-C₆₀ heteroaryl alkyl group,a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—Ge(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇), —P(Q₂₈)(Q₂₉),—P(—0)(Q₂₈)(Q₂₉), or a combination thereof; or —Si(Q₃₁)(Q₃₂)(Q₃₃),—Ge(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇), —P(Q₃₈)(Q₃₉), or—P(=O)(Q₃₈)(Q₃₉), and Q₁ to Q₉, Q₁₁ to Q₁₉, Q₂₁ to Q₂₉, and Q₃₁ to Q₃₉are each independently hydrogen, deuterium, —F, —Cl, —Br, —SF₅, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₁-C₆₀alkylthio group, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group,a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted heterocycloalkenyl group, a substituted or unsubstitutedC₆-C₆₀ aryl group, a substituted or unsubstituted C₇-C₆₀ alkyl arylgroup, a substituted or unsubstituted C₇-C₆₀ aryl alkyl group, asubstituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted orunsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstitutedC₁-C₆₀ heteroaryl group, a substituted or unsubstituted C₂-C₆₀ alkylheteroaryl group, a substituted or unsubstituted C₂-C₆₀ heteroaryl alkylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryloxy group, asubstituted or unsubstituted C₁-C₆₀ heteroarylthio group, a substitutedor unsubstituted monovalent non-aromatic condensed polycyclic group, ora substituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group.
 2. The organometallic compound of claim 1,wherein M₁ is iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti),zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm),or rhodium (Rh).
 3. The organometallic compound of claim 1, wherein M₁is Ir, and a sum of n1 and n2 is
 3. 4. The organometallic compound ofclaim 1, wherein ring CY₁ and ring CY₂ are each independently a phenylgroup, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, aphenanthrene group, a pyridine group, a pyrimidine group, a pyrazinegroup, a triazine group, a quinoline group, an isoquinoline group, aquinoxaline group, a quinazoline group, a phenanthroline group, abenzofuran group, a benzothiophene group, a fluorene group, a carbazolegroup, a dibenzofuran group, a dibenzothiophene group, a dibenzosilolegroup, a dibenzoselenophene group, an azafluorene group, an azacarbazolegroup, an azadibenzofuran group, an azadibenzothiophene group, anazadibenzosilole group, or an azadibenzoselenophene group.
 5. Theorganometallic compound of claim 1, wherein ring CY₃ is a pyridinegroup, a pyrimidine group, a pyrazine group, a pyridazine group, atriazine group, a quinoline group, an isoquinoline group, abenzoquinoline group, a benzoisoquinoline group, a phenanthroline group,a quinoxaline group, or a quinazoline group, and Ring CY₄ is a phenylgroup, a naphthalene group, a pyridine group, a pyrimidine group, apyrazine group, a pyridazine group, a triazine group, a quinoline group,an isoquinoline group, a benzoquinoline group, a benzoisoquinolinegroup, a phenanthroline group, a quinoxaline group, or a quinazolinegroup.
 6. The organometallic compound of claim 1, wherein Ln1 isrepresented by Formula 1A-1 or 1A-2:

wherein, in Formulae 1A-1 and 1A-2, Y₁ is O, S, Se, orC(R_(29A))(R_(29B)), X₁₁ is C(R₁₁) or N, X₁₂ is C(R₁₂) or N, X₁₃ isC(R₁₃) or N, and X₁₄ is C(R₁₄) or N, X₂₁ is C(R₂i) or N, X₂₂ is C(R₂₂)or N, X₂₃ is C(R₂₃) or N, and X₂₄ is C(R₂₄) or N, X₂₅ is C(R₂₅) or N,X₂₆ is C(R₂₅) or N, X₂₇ is C(R₂₇) or N, and X₂₈ is C(R₂₈) or N, R₁₁ toR₁₄ are each independently as described in connection with R₁₀ in claims1, R₂₁ to R₂₈, R_(29A), and R_(29B) are each independently as describedin connection with R₂₀ in claim 1, and * and *′ each indicate a bindingsite to M₁. 7 The organometallic compound of claim 6, wherein Y₁ is O orS.
 8. The organometallic compound of claim 1, wherein Ln₂ is representedby Formula 1B-1:

wherein, in Formula 1B-1₇ X₃₁ is C(R₃₁) or N, X₃₂ is C(R₃₂) or N, X₃₃ isC(R₃₃) or N, and X₃₄ is C(R₃₄) or N, X₄₁ is C(R₄₁) or N, X₄₂ is C(R₄₂)or N, X₄₃ is C(R₄₃) or N, and X₄₄ is C(R₄₄) or N, R₃₁ to R₃₄ are eachindependently as described in connection with R₃₀ in claims 1, R₄₁ toR₄₄ are each independently as described in connection with R_(4.0) inclaim 1, and * and *′ each indicate a binding site to M₁.
 9. Theorganometallic compound of claim 1, wherein Y₂ is O.
 10. Theorganometallic compound of claim 1, wherein R₁₀, R₂₀, R₃₀, and R₄₀ areeach independently: hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, —CD₃,—CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₁-C₆₀ alkylthiogroup, —Si(Qi)(Q₂)(Q₃), or —Ge(Q₁)(Q₂)(Q₃); or a group represented byone of Formulae 9-1 to 9-67, 9-201 to 9-244, 10-1 to 10-154, or 10-201to 10-350:

wherein, in Formulae 9-1 to 9-67, 9-201 to 9-244, 10-1 to 10-154, and10-201 to 10-350, * indicates a binding site to a neighboring atom, “Ph”is a phenyl group, “TMS” is a trimethylsilyl group, and “TMG” is atrimethylgermyl group.
 11. The organometallic compound of claim 1,wherein at least one of R₁₀, R₂₀, R₃₀, and R₄₀ is a methyl group, anethyl group, an n-propyl group, an isopropyl group, an n-butyl group, anisobutyl group, a sec-butyl group, a tert-butyl group, an n-pentylgroup, an isopentyl group, a 2-methylbutyl group, a sec-pentyl group, atert-pentyl group, a neo-pentyl group, a 3-pentyl group, a3-methyl-2-butyl group, a cyclopentyl group, or a cyclohexyl group. 12.The organometallic compound of claim 1, wherein the organometalliccompound is a compound represented by one of Formulae 30-1 and 30-2:

wherein, in Formulae 30-1 and 30-2, M₁, n1, n2, and Y2 are as describedin claim 1, Y₁ is O, S, Se, or C(R_(29A))(R_(29B)), R₁₁ to R₁₄ are eachindependently as described in connection with R₁₀ in claim 1, R₂₁ toR₂₈, R_(29A), and R_(29B) are each independently as described inconnection with R₂₀ in claim 1, R₃₁ to R₃₄ are each independently asdescribed in connection with R₃₀ in claim 1, and R₄₁ to R₄₄ are eachindependently as described in connection with R₄₀ in claim
 1. 13. Theorganometallic compound of claim 1, wherein the organometallic compoundis electrically neutral.
 14. The organometallic compound of claim 1,wherein the organometallic compound is one of Compounds 1 to 30:


15. An organic light-emitting device comprising: a first electrode; asecond electrode; and an organic layer located between the firstelectrode and the second electrode, wherein the organic layer comprisesan emission layer, and wherein the organic layer comprises at least oneof the organometallic compound of claim
 1. 16. The organiclight-emitting device of claim 15, wherein the emission layer comprisesthe at least one of the organometallic compound.
 17. The organiclight-emitting device of claim 16, wherein the emission layer furthercomprises a host, and an amount of the host in the emission layer isgreater than an amount of the organometallic compound in the emissionlayer.
 18. The organic light-emitting device of claim 16, wherein theemission layer emits green light having a maximum emission wavelength ina range of about 490 nanometers to about 550 nanometers.
 19. The organiclight-emitting device of claim 15, wherein the first electrode is ananode, the second electrode is a cathode, the organic layer furthercomprises a hole transport region located between the first electrodeand the emission layer, and an electron transport region located betweenthe emission layer and the second electrode, the hole transport regioncomprises a hole injection layer, a hole transport layer, an electronblocking layer, a buffer layer, or a combination thereof, and theelectron transport region comprises a hole blocking layer, an electrontransport layer, an electron injection layer, or a combination thereof.20. An electronic apparatus, comprising the organic light-emittingdevice of claim 15.